Jack Pilla Has Become an Ultrarunning Star at 51

A difficult divorce turned him on to running, and a whole new world

In every 100-mile race, there is at least one dark, unforgivably depressing section when it's all a runner can do to continue. It's a space of time and trail, where personal demons lurk behind boulders and trees partner with doubt and pain to assault a runner's will. An aspect of the ultra world that stands apart from most running experiences, surviving these emotional forays into the gutter of despair is an art best practiced by those with some history on their shoulders.

Nine years ago, Jack Pilla became a runner. On the tail end of a difficult divorce, he was told by a friend to try a marathon. With little more than four weeks of training under his belt, Pilla jumped into the Vermont City Marathon and cranked out a 3:19. During the race, his IT band locked up on him so badly that he could barely walk for days afterward. But the marathon was something he liked, and he decided to do more of them. "Running became a way to deal with some of the stress with what I was going through with my family," he says.

On the road to relief, Pilla has run dozens of marathons and become a dominant force in the ultra world with wins at the Stone Cat 50, the Finger Lakes Fifties and last year's first-place finish at the Vermont 100 Endurance Race at age 51, the oldest man to win that event.

In the Vermont 100, he was running shoulder to shoulder with Pennsylvania's Jason Lantz until the 88-mile mark. Finally, he broke free from the 28-year-old and, over the next 12 miles, put almost 45 minutes into his lead. Pilla ignored his pacer's late-stages good humor when victory was clearly in hand and instead pushed hard to the finish, becoming the first Vermonter to win the event. This season Pilla will defend his title in Vermont and also compete in the Leadville 100.

Heading out past vegetable and flower gardens, with Lake Champlain and the Adirondacks in the distance, Pilla runs from his property and onto a nearby wildlife preserve. His 4-mile morning loop serves as either a wake-up call or the start of a much longer run. He likes to get his run in first thing, because it "gets oxygen" to his brain. His workouts are loosely structured, averaging 70-100 miles a week with regular speed and hill sessions. Living just outside of Burlington in Vermont's Green Mountains, vertical work is impossible to avoid, not that he ever wants to. One of his favorite nearby slopes is aptly named "Puke Hill." This is a man unafraid to push his limits.

Growing up on Long Island, Pilla was an indifferent athlete when it came to organized sports. A brief wrestling stint was quickly forgotten in a search for smooth pavement and big waves as his passion for skateboarding and surfing grew. The only sign of what he would someday accomplish as a runner was a favorite pastime developed in the cramped back yards of his neighborhood. Like a dog with a stolen bone in his mouth, the diminutive Pilla would race through the yards, creating trails on the fly while trying to outpace the heated reactions of the trespassed homeowners. It's a memory that still brings a devilish grin to his weathered face. "I don't know why I did it, just something to do," he laughs.

Whether in a neighbor's yard or the mountains surrounding his Vermont home, Pilla has a clinical approach to learning his body's capabilities. Last summer, for example, he banged out a hot 20-mile run with a single water stop at the halfway point, "just to see what it would be like," he explains, then deadpans, "I wouldn't recommend it."

To test his fitness before a 100-miler, Pilla has taken to doing an unsupported out-and-back 46-miler on New Hampshire's Presidential Range. Known for having the "worst weather on earth," where a sunny 70-degree day can quickly become a howling blast of meteorological misery, the range contains a dozen mountains, almost 20,000 feet of climbing and not a smooth step the entire way. And while completing the run has been a good barometer for race-day performance, it does come with some serious risks. "There was one time I finished it and then got in my car to drive home. But first I needed something to eat," Pilla says, explaining his trip to a roadside diner. Arriving there, he recalls, "Every time I thought I'd put the car in park to get out, I'd fall asleep, wake up and see I was still in gear and rolling through the parking lot." Eventually, the need for rest overcame his hunger, and he got in the back of the car and slept.

To fill part of the void left by his divorce, Pilla has found a place in the robust running community of greater Burlington. He publishes the Green Mountain Athletic Club's newsletter and, with his 50-and-over club-mates, won the 2009 national cross country team title for that age group. Recently, Pilla became certified as a running coach: "Satan" is how his first client likes to refer to him. The workouts he prescribes are difficult; they reflect the pain necessary to succeed, pain Pilla learned from the hardships faced away from competition.

Pilla had to leave his three children after his divorce and has not seen them since. It's a pain that, for him, has no equal. Asked how he deals with his dark moments on the trail, he is quiet for a time. Then, with his eyes on the breakfast plate before him and in a voice just loud enough to be heard over the hustle of a Sunday restaurant, he shares one of the secrets to his strength: "I have a little frog trinket from my kids that I wear on my belt when I'm racing. When it hurts, I hold on to that frog and I know that if I can get through not seeing them, I can make it through anything."